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"Mr. Burns tries to relive his glory days, and crosses paths with a mysterious music mogul. Burns is then conned by him and reduced to bankruptcy. Also, Lisa is courted by the richest kid in town and Smithers begins a perilous journey."

Mr. Burns is reminiscing about his youth, while receiving a double shot of fresh blood. To relive part of it, Smithers suggests a party at his Summer Mansion in Middle Hampton. Instead of store-bought ice, Burns cheaps out and sends Smithers to Canada to bring some lake ice.

Arriving at the mansion, however, they find out that Burns has cheaped out again, and the party is so boring they leave. While Smithers is having some trouble on a raft in Canada, Homer consoles Burns at the pier. They spot a party across the lake at a Mansion so they cross over in a rowboat, Burns inciting Homer with a whip.

The two arrive at the party, trying to crash it, and discover that the host, Jay G, likes Mr. Burns as he is his role model. Jay G thanks Burns for making him become who he is.

Meanwhile, Marge, Lisa, Bart and Maggie visit the city and go to an ice cream shop where Lisa meets Blake, a spoiled rich kid who wants to hang out with her. She eventually agrees to meet him while Bart meets a mysterious candle vendor (Jazzy James), who narrator-Homer thinks "comes back later" but forgets why.

Jay G brings Homer and Burns on his private plane and gives Burns a special credit card (the "Obsidian Card") for extravagant spending. Meanwhile, Blake and Lisa go whale watching but Blake's brutal means to bring the whales near the boat makes Lisa positively furious.

Jay G invites Burns, with Homer tagging along, to buy a lot of stuff for really high prices, and slowly empties out his bank account. The rest of the family meets Blake again at a horse show and Lisa is delighted to find he's turned over a new leaf and become a protestor for horse justice. But when another boy offers her grooming time with the horses, she can't resist and accepts, dumping Blake.

In Canada, Smithers' misadventures continue. When trying to answer Burns' call, he breaks his phone and loses his glove. Burns soon finds out his troubles are worse when his Obsidian card is declined, as he is broke. Repossessors come to his mansion to retrieve all his expensive belongings and Homer shows him that Jay G purposely conned him into bankruptcy (detailed in the lyrics of Jay's new rap video). Burns is reduced to tears after finding out, hitting rock bottom.